Automattic Chief Quality Officer, Lance Willett, on What It Takes to Power 45% of the Web and Learning from a $250K Mistake

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/cooGuest: Lance Willett, Chief Quality Officer at AutomatticTopics Covered:How Automattic’s open source culture evolved over 20 yearsWhat a Chief Quality Officer actually does—and why it mattersQuality = Craft × Context, and how that feedback loop scalesAutomattic’s AI strategy: support bots, contextual UI, and site generationThe importance of tools like Linear and Storybook in enforcing qualityHow Automattic balances speed, risk, and governance with AI experimentationLessons from stabilizing Tumblr during its post-acquisition rebootPrioritization and the dangers of unbounded optimismLeadership takeaways from working closely with Matt Mullenweg🕰️ Time Map00:00 – 03:00: Intro and Lance’s journey from freelancer to Automattic03:00 – 06:30: How Automattic’s open source ethos evolved over 20 years06:30 – 10:30: What it means to be a Chief Quality Officer—Craft × Context10:30 – 15:00: Scaling quality: repo sprawl, signal vs. noise, and auditing15:00 – 20:00: UX details like forms, performance, and speed as quality levers20:00 – 24:00: Driving culture change with standard tooling (Linear, Storybook)24:00 – 28:00: Guardrails for AI experimentation and internal governance28:00 – 32:00: AI at Automattic: support bots, contextual UI, AI site builder32:00 – 36:00: Competing with Webflow, Wix, and Squarespace through innovation36:00 – 38:30: Balancing ecosystem contribution with revenue and investor pressure38:30 – 41:00: Lessons from stabilizing Tumblr: cost, culture, safety, turnover41:00 – 44:00: Automattic’s long-term challenge: bounded optimism and focus44:00 – 46:30: Leadership wisdom from Matt Mullenweg: details always matter46:30 – 49:00: Lance’s $250K mistake—and what it taught him about leadership https://brodo.com/ (our other sponsor 😂)https://fullstackleader.blog/ (work topics: WordPress, tech, productivity, quality, & more)https://lance.blog/ (fun stuff: poems, stories, links; photos “on the go”)https://linear.app/https://clay.earth/ via https://automattic.com/2025/06/12/automattic-welcomes-clay/ Companies with dedicated quality efforts:https://anthonyhobday.com/blog/20240914.html > While fixing small bugs might not 10x your growth overnight> Not fixing them will make 10x growth impossible over timeCredit: Casey Winters – someone you should have on this show if you haven’t alreadyhttps://caseyaccidental.com/ Episode webpage - https://www.betweentwocoos.com/automattic-chief-quality-officer-lance-willett-wordpressMichael Koenig - https://linkedin.com/in/michael-koenig514 Between Two COO's - https://betweentwocoos.com